The present invention is relative to novel amino-2 aryloxymethyl-5 oxazolines, as well as to their salts with pharmacologically compatibles acids.
The compound according to the invention have the general formula: ##STR2## wherein Ar is a phenyl-2 phenyl, phenyl-3 phenyl or phenyl-4 phenyl group.
The compounds according to the invention are prepared by condensation of aryloxy-1 epoxy-2,3 propanes having the structure II ##STR3## wherein Ar has the same meaning as hereinabove, with a sodium monocyanamide in an organic solvent soluble in water, as the lower alcools in C.sub.1 to C.sub.4, e.g. methanol, ethanol, isopropanol or butanol, or as tetrahydrofuran or dimethylformamide, and at a temperature between 0.degree. C. and 80.degree. C.
The compounds having structure II are well known, and their preparations are disclosed in U.S. Pat. No. 2,181,085 assigned to DOW CHEMICAL COMPANY.
The Assignee has already disclosed in French patents 2533922 and 2546167 amino-2 aminomethyl-5 oxazolines.
JARRY et al. have disclosed in Bull. Soc. Pharm. Bordeaux, 1981, 120, 153-162 aryloxymethyl-5 amino-2 oxazolines having structure III, ##STR4## wherein group R is a methyl group in position 4, chlorine in position 4, methoxy in position 4, an acetamido group in position 4, or allyl in position 4 and methoxy in position 2, or group R is a CH=CH-CH=CH group in 2,3 and constitutes with the benzene cycle a naphtyl-1 group. These compounds have interesting antihypertension properties.
DOW CHEMICAL has described in U.S. Pat. No. 3,637,726 assigned to said corporation (dihalo-3,4 phenoxy)methyl-5 amino-2 oxazolines having structure IV ##STR5## wherein X represents an halogen atom, as chlorine or bromine. These compounds enjoy interesting antimicrobial properties.